In case you haven't come to realize the psychology behind snobbery at this point in your life, snobs usually resort to snobbery because they hate the idea they were once a novice. They so despise being looked down upon, that they go out of their way to be the one looking down. They want to separate themselves as far as humanly possible from the newcomer, the guy who's out-of-the-loop, and there's no better way to do that than to act like a snob – in essence, they're trying to show you how far they've come. The irony of snobbery, however (besides the obvious reality that we all were novices at some point) is the fact that many of the worst snobs are usually far from knowledgable. The snobbery itself is a shield against their own insecurities, a manifestation of the idea that the best defense is a good offense – hence, the pedantic way in which they need to prove themselves.

When I first watched Sideways back in 2005, I was a budding wine enthusiast. I didn't know much about wine and I didn't have much money to spend on discovering it, but I liked the idea of it. Watching a movie about wine only increased my enthusiasm. I saw how passionate Miles was about pinot noir and I thought, "Here's a guy who loves wine, cares about wine, and knows a lot about it. I wish I cared that much about it." That's what I thought back then. Having watched Sideways again this past weekend, however, I have a much different persepctive after six years in the wine business: I now realize that Miles is an obnoxious snob who embodies the worst parts of this hobby. His snobbish attitudes on wine stem from a fear of his own basic inadequacies. What's amazing to me now is how accurately the film portrays these pathetic character flaws and how well developed their roots are. The script reads like a case study in the origins of booze pedantry.

It's no secret that Miles is an anxious, insecure, pessimistic guy. That part was clear to me eight years ago. What I didn't catch back then, however, was how he uses his wine knowledge to bully his friend, buoying his ego against Jack's good looks and natural charm. When they first hit the road towards the Central Coast, Jack reaches back to grab a sparkling wine, which Miles describes as "100% pinot noir." When Jack pops the bottle and pours himself a glass, to Miles's complete dismay, he asks why the wine is white if it's made from pinot noir. Immediately, Miles rolls his eyes, sneers, and says: "Don't ask those kind of questions when we get up to wine country; they'll think you're some sort of dumbass." Obviously, there was a point in time when Miles didn't understand the concept of skin color maceration either, but instead of simply telling his friend why the red grape produced a white wine, he first took the opportunity to belittle Jack's naiveté. That's some Wine Snob 101 right there: explain your knowledge only after you point out how little the other person knows.

What becomes clear, however, upon their arrival to wine country is that Miles isn't as much of an expert as he wishes he was. He definitely wants Jack to think of him as such though, so he continues to put on the charade. When they walk into the Hitching Post in Buellton, Miles says with faux casualty, "This is where I eat when I come here. It's practically my office." This comment is also an example of classic wine snobbery in that it paints Miles as someone "in-the-know" – an insider with all the locals. The bartender recognizes him as he sits down and it's clear that Miles is revelling in this. When he tastes the new vintage of pinot noir at the bar, he instantly says, "Tighter than a nun's asshole. Good fruit," as a seeming compliment to the wine's flavor. "Tight," however, is how we describe a wine with little flavor – a wine that needs time in the cellar to unravel and reveal its potential for splendor. It's not necessarily a negative descriptor, it just means the wine isn't quite ready to be consumed. It seems that Miles is simply parroting a term he's picked up in a local tasting bar, hoping to sound more educated in front of a true wine professional. What's even funnier is that Jack immediately chimes in, not wanting his silence to be mistaken for stupidity: "Yeah.......it's tight."

Back in 2005, I had no idea what "tight" meant, just like I wasn't as aware of Miles's profound snobbish behavior. I was just a guy enjoying a movie about wine. Today, however, I see that type of act in tasting bars everywhere: guys talking loudly about the brix level of the grapes, making bold assessments of the vintage, contradicting the authority opinion to make themselves sound more knowledgeable in return. With my six years of exposure to this type of personality, my respect for Paul Giamatti's acting job has gone way, way up. He's absolutely nailed the insecure wine snob, right down to the facial expressions. One of my new favorite moments from the film is when Mya and Miles decide to open a bottle of Andrew Murray Syrah. Miles swirls, smells, tastes and declares: "Oh wow. We need to give it a minute, but it's there alright." Mya isn't as needy as Miles, however, and doesn't have the chip on the shoulder he does. She's more thoughtful and observant: "I don't know," she counters, "I think they overdid it. Too much alcohol masks the fruit." All of a sudden, Miles changes direction, tastes again, and totally jumps ship to side with Mya's perspective. "Yeah," he says, "I'd say you're spot on. Very good." It's clear that Miles often has an opinion simply to have one, but can be swayed easily or overruled by a more authoritative voice because ultimately he's unsure of himself.

Perhaps the most telling moment of the film, however, is when Miles learns his last chance at a book deal for his novel has been rejected. After making a gigantic scene with the winery dump bucket, he sits with Jack at a picnic table outside and says, "The world doesn't give a shit about what I have to say. I'm unnecessary. Half my life is over and I have nothing to show for it." This scene really resonated with me because, ultimately, that's what I feel the core of snobbery is: a desire to be listened to, for people to pay attention to you, to be the real expert that the world should be recognizing, but isn't. If we didn't care so much about people's opinions of us (or of others for that matter), there would be no need for snobbery, or pedantry, or attention-seeking behavior. That's pretty much the root of it. Miles's biggest fear is that he'll end up meaningless in the game of life, as merely "a thumbprint on the window of a skyscraper." Half of the people who criticize guys like Robert Parker do so not out of any real disagreement, but because ultimately they're upset no one's listening to them. They're afraid that no one cares about what they think or values their opinions, so they continuously make us aware of them. The movie captures that mentality honestly and sincerely, in a fashion that I never could have appreciated back then.

As someone who writes a blog, I get a bit nervous watching Miles because there are many things about him that I recognize in myself – those same desires for attention and for people to like what I have to say. It's embarrassing to think about them, and even more embarrassing to write about them here – publicly. Ultimately, however, I like to think that I've learned from watching people like Miles exactly what not to do and how not to behave when it comes to wine appreciation. One of my colleagues once told me, "I couldn't watch Sideways, not because it was a bad film, but because it was too good and accurate of a film." I completely understand that opinion today. However, it's nice to revisit the movie now and again, if not for the sheer entertainment of the adventure, then for the sheer brilliance of how it explains the mentality of the wine snob, why he is who he is, with all of his innermost insecurities on display.